Any cashflow from STR is a bonus on top.Does this plan seem logical?

Bonus points if actually compliant with prevailing local and HOA regs. 

I already had all the team in place from other projects (architecture, civil, structural, soils, geology, survey, historical) ... we've been at it for 9 months and we haven't even submitted final construction docs.That's one anecdotal example, but the pattern is clear - whether it's CEQA or Historical or riparian habitat or community plan or setbacks or parking or mixed use bonus that hits the FAR ceiling or phantom floors or utility undergrounding, there's just a lot to understand if you're trying to build anything more than a duplex on a single property within City limits.I only have development experience in SD City limits ... curious if anyone has experience doing this in surrounding jurisdictions (La Mesa?  

Bonus if it's NOT in a part of the country that gets snow. 

I'm giving you the IT job, consider this a signing bonus."

The other bonus with multi-family is that a lot of people rent them out for a lot lower than market.  

The study identifies with forensic engineering detail the immediate Bonus Depreciation 5, 7 and 15-year personal property class lives qualifying portions of a building that are normally buried in 27.5 year residential or 39 year commercial categories.The Cost Segregation Study was performed on the Asset Depreciation Range (ADR) and is based on a 40% tax bracket for State and Federal Taxes.

On the MLS you will see words like "excercise room" "bonus room" "finished basement with walkout space" kinda thing.

So, the property drop just increased my cash flow, without raising the rent.The beauty of this method is two fold:1 - You never ever spend the principle, since every refi allows you to get it back.2 - You never need another source of funds, since you can use the same funds until your arm gets tired.3 - Ok, I said two, think of this a a big bonus.  

Also, you want to search for other terms, like guest house, bonus room, mother-in-law suite, separate living quarters, etc.